2-Chloro-N,N-dimethylethylamine → 2-(p-Isobutylphenyl)propionic acid dimethylaminoethyl ester

HRID 26447

Reaktionsgleichung

Reaktionsgleichung von HRID 26447
[Na+].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:16])[C:13]([O-:15])=[O:14])=[CH:8][CH:7]=1)[CH:3]([CH3:5])[CH3:4].[CH3:17][N:18]([CH2:20][CH2:21]Cl)[CH3:19]>C1C=CC=CC=1>[CH3:17][N:18]([CH2:20][CH2:21][O:14][C:13](=[O:15])[CH:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:2][CH:3]([CH3:5])[CH3:4])=[CH:11][CH:10]=1)[CH3:16])[CH3:19]

Komponenten

4

Edukt 2

HCID 79012-Chloro-N,N-dimethylethylamineHCID 5338317Ibuprofen, Sodium Salt

Produkt 1

HCID 136019482-(p-Isobutylphenyl)propionic acid dimethylaminoethyl esterAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 3.3 g of 2-(p-isobutylphenyl)propionic acid sodium salt, 2.3 g of dimethylaminoethyl chloride and 30 ml of benzene was refluxed for 12 hours. A solid mass produced was filtered off, and the benzene was distilled away from the filtrate under reduced pressure to leave an oily residue. This redidue was distilled under reduced pressure to give 3.5 g of 2-(p-isobutylphenyl)propionic acid dimethylaminoethyl ester as a colorless oil, boiling at 133°-136° C./1 mmHg. Analysis-Calculated for C17H27NO2 : C, 73.61; H, 9.81; N, 5.05. Found: C, 73.50; H, 9.72; N, 5.02. The infrared spectrum showed strong C=O absorption at 1730 cm-1 characteristic for ester. Mass spectrum: parent ion 277 m/e.

Aufarbeitung

  1. temperaturewas refluxed for 12 hours
  2. customA solid mass produced
  3. filtrationwas filtered off
  4. distillationthe benzene was distilled away from the filtrate under reduced pressure
  5. customto leave an oily residue
  6. distillationThis redidue was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ef2503e9a937472aafda45fcee7cd763
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04150137

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